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A versatile and green synthetic protocol has been developed for synthesis of substituted quinazolinone and spiroquinazolinone heterocycles effectively via a combined surfactant mediated system. The use of Surfactant, water as reaction medium, room temperature, high yield and ease of purification made the process very effective and ecofriendly in nature. To demonstrate the wide scope of reaction Isatoic anhydride and Isatin used as reactants in different sets of reactions that leads to formation of Quinazolinones and spiroquinazolinones. A total of 12 derivatives has been prepared and characterized by all the spectroscopic data. The developed protocol presents a better and environmentally efficient methodology to get these heterocycles.

References

  1. Andrade C K Z, Alves L M, Environmentally Benign Solvents in Organic Synthesis, Curr. Org. Chem. 2005; 9, 195–218. doi:10.2174/1385272053369178.
     Google Scholar
  2. Chanda A, Fokin V V, Organic Synthesis “On Water” Chem. Rev. 2009; 109, 725–748. doi:10.1021/cr800448q.
     Google Scholar
  3. Lindstrom U M, Stereoselective Organic Reactions in Water, Chem. Rev. 2002; 102, 2751–2772. doi:10.1021/cr010122p.
     Google Scholar
  4. Shiri M, Zolfigol M A, Surfactant-type catalysts in organic reactions, Tetrahedron, 2009; 65, 587–598. doi:10.1016/j.tet.2008.09.085.
     Google Scholar
  5. Tuch AM, Wallé S, Nicolaou K C, Hanko R, Hartwig W, Multicomponent Reactions. In Handbook of Combinatorial Chemistry; Eds.; Wiley-VCH: Weinheim, Germany, 2002, Vol. 2, pp 685–705.
     Google Scholar
  6. Guo D, Zhu D, Zhou X, Zheng B, Understanding “On-Water” Catalysis of Organic Reactions, Langmuir, 2015, 31(51), 13759–13763.
     Google Scholar
  7. Nakadai M, Saito S, Yamamoto H, Diversity-based strategy for discovery of environmentally benign organocatalyst: diamine–protonic acid catalysts for asymmetric direct aldol reaction, Tetrahedron Letters, 2002; 58(41), 8167-8177.
     Google Scholar
  8. Domling A, Ugi I, Multicomponent Reactions with Isocyanides, Angew. Chem. Int. Ed. 2000; 39, 3168.
     Google Scholar
  9. Domling, A. Recent Developments in Isocyanide Based Multicomponent Reactions in Applied Chemistry, Chem. Rev. 2006; 106, 17.
     Google Scholar
  10. Hossain N, Rozenski J, Clercq ED, Herdewijn P, Synthesis and antiviral activity of the alpha-analogues of 1,5-anhydrohexitol nucleosides, J. Org. Chem. 1997; 62, 2442.
     Google Scholar
  11. Hargreaves SL, Pilkington BL, Russell SE, Worthington PA, The synthesis of substituted pyridylpyrimidine fungicides using palladium catalysed cross-coupling reactions. Tetrahedron Lett. 2000; 41,1653–1656.
     Google Scholar
  12. Sainath ZB, Quinazoline Based Synthesis of some Heterocyclic Schiff Bases, Book chapter Intech open, DOI: http://dx.doi.org/10.5772/intechopen.89871.
     Google Scholar
  13. Yung Y, Lee SB, Junhwa H., Simin C., Hong LJ, Synthesis of 2-aryl quinazolinones via iron-catalyzed cross-dehydrogenative coupling (CDC) between N–H and C–H bonds, Organic and Biomolecular Chemistry, 2020; 18(28), 5435-5441.
     Google Scholar
  14. Li D, Wei T, Weng H, Ghandi W, Zeng K, A recyclable CuO-catalyzed synthesis of 4(3H)-quinazolinones, RSC Advances, 2013; 3(24), 9325-9329.
     Google Scholar
  15. Aniket VA, Maity, Schulzke S, Maiti C, Kapdi D, Anant R, Synthesis of Cu-catalysed quinazolinones using a Csp3–H functionalisation/cyclisation strategy, Organic and Biomolecular Chemistry, 2017, 15(34), 7140-7146.
     Google Scholar
  16. Qian, Allegretta Y, Janardhanan G, Peng J, Mahasenan Z, Kiran V, Lastochkin, Gozun E, Malia M, Tejera N, Sara Schroeder, Valerie A. Wolter, William R. Feltzer, Rhona Mobashery, Shahriar Chang, Mayland, Exploration of the Structural Space in 4(3H)-Quinazolinone Antibacterials, Journal of Medicinal Chemistry, 2020; 63(10), 5287-5296.
     Google Scholar
  17. Kshirsagar UA, Recent developments in the chemistry of quinazolinone alkaloids, Org. Biomol. Chem., 2015; 13, 9336-9352.
     Google Scholar
  18. Khan, Ibrar I, Abbas A, Saeed N, Aamer, Recent advances in the structural library of functionalized quinazoline and quinazolinone scaffolds: Synthetic approaches and multifarious applications, European Journal of Medicinal Chemistry, 2014; 76, 193-244.
     Google Scholar
  19. Desai NC, Amit M, Synthesis, characterization and antimicrobial screening of quinoline based quinazolinone-4-thiazolidinone heterocycles, Arabian Journal of Chemistry, 20147; 6, 906-913.
     Google Scholar
  20. Mishra, Mukherjee A, Vats U, Deb TK, Indubhusan, Ir(III)/MPAA-Catalyzed Mild and Selective C–H Amidation of N-Sulfonyl Ketimines: Access To Benzosultam-Fused Quinazolines/Quinazolinones, Journal of Organic Chemistry, 2018; 83(7), 3756-3767.
     Google Scholar
  21. Connolly, Cusack DJ, O'Sullivan D, Guiry TP, Synthesis of quinazolinones and quinazolines, Tetrahedron, 2005; 61(43), 10153-10202.
     Google Scholar
  22. Tripathi VD, Jha AM, Design and Synthesis of Heterocyclic Curcumin Analogues as Filarial Topoisomerase II Inhibitors, J. Bio. Chem. Chron., 2018; 4, 59-64.
     Google Scholar
  23. Tripathi VD, Shukla AK, Design and Synthesis of Novel Heterocyclic Curcumin Analogues as Anticancer Agents and Filarial Topoisomerase II Inhibitors, Asian J. Org. Med. Chem., 2018; 3(4), 164-170.
     Google Scholar
  24. Kumar A, Kumar P, Tripathi VD, and Srivastava S, A novel access to indole-3-substituted dihydrocoumarins in artificial sweetener saccharin based functional ionic liquids, RSC Advances, 2012; 2, 11641–11644.
     Google Scholar
  25. Tripathi VD, Shukla AK, and Mohammed HS, Regioselective Three Component Domino Synthesis of Polyhydrospiro[indoline-3,3'-pyrrolizine]-2-one via [3+2] Cycloaddition Reaction, Asian Journal of Chemistry; 2019; 31, 613-616.
     Google Scholar
  26. Tripathi,VD, Β-Cyclodextrin mediated multicomponent synthesis of spiroindole derivatives in aqueous medium, Asian Journal of Chemsitry, 2020; 32(2), 293-296.
     Google Scholar
  27. Kumar A, Tripathi VD, Kumar P, β-Cyclodextrin catalysed synthesis of tryptanthrin in water, Green Chemistry, 2011; 13, 51-54.
     Google Scholar